4-(N-Boc-amino)piperidine → tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate

HRID 2233891Notes

Reaction equation

HRID 2233891 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C([N:32]=[C:33]=[S:34])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>C(Cl)Cl>[NH2:32][C:33]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)=[S:34]

Participants

4

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 4154759Fmoc isothiocyanate

Product 1

HCID 59296117tert-butyl N-(1-carbamothioylpiperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl piperidin-4-ylcarbamate (5.5 g) was dissolved in anhydrous DCM (75 ml). H-Fluoren-9-ylmethyl isothiocyanatidocarbonate (Fmoc isothiocyanate; 7.75 g) was added in small portions at room temperature after which time a white precipitate formed. The mixture was stirred at room temperature for 90 min. The solvent was removed in vacuo and the crude mixture was treated with 10% piperidine in MeOH (100 ml) for 12 h. The mixture was concentrated in vacuo and triturated with n-hexanes. The white crystalline material was filtered and washed well with n-hexanes and dried in vacuo to afford the title compound (6.55 g).

Workup

  1. additionwas added in small portions at room temperature after which time a white precipitate
  2. customformed
  3. customThe solvent was removed in vacuo
  4. additionthe crude mixture was treated with 10% piperidine in MeOH (100 ml) for 12 h
  5. concentrationThe mixture was concentrated in vacuo
  6. customtriturated with n-hexanes
  7. filtrationThe white crystalline material was filtered
  8. washwashed well with n-hexanes
  9. customdried in vacuo

Sources & evidence

ORD record
ord-72926c0533ae4869a5d8b23b1f4e1ed6
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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